(R)-N-(1-phenylpropyl)formamide | 439271-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-N-(1-phenylpropyl)formamide
• 英文别名: (S)-N-(1-phenylpropyl)formamide；N-(1-phenylpropyl)formamide；N-(1-Phenyl-propyl)-formamide；N-[(1R)-1-phenylpropyl]formamide
• CAS: 439271-80-4
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: UERJGKDKJBSKQN-SNVBAGLBSA-N

物化性质

• 熔点：
  56.8-58.8 °C
• 沸点：
  326.6±21.0 °C(Predicted)
• 密度：
  1.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-phenylpropyl)formamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 (R)-(+)-1-苯丙胺
  参考文献：
  名称：

  [2.2]对环芳基N,O-配体催化不对称二烷基锌加成亚胺

  摘要：

  据报道，在催化量的 N,O-配体存在下，首次对亚胺具有高度对映选择性的二烷基锌加成。N-甲酰基-α-（对甲苯磺酰基）苄胺是容易获得的起始原料，可通过苯甲醛、甲酰胺和对甲苯基亚磺酸一锅法合成。去质子化后，亚磺酸盐被消除，得到酰基亚胺。在催化量的基于 [2.2] 对环芳烷的 N,O-配体 L 的存在下，酰基亚胺进一步与烷基锌试剂反应，产生具有优异产率和对映选择性的烷基化 N-（1-苯丙基）甲酰胺。

  DOI：

  10.1021/ja025831e
• 作为产物：
  描述：

  甲酸 、 (R)-(+)-1-苯丙胺 在 乙酸酐 作用下， 以96%的产率得到(R)-N-(1-phenylpropyl)formamide
  参考文献：
  名称：

  Chain branching approach in structure modification of TRPV1 receptor antagonist MK056 and its analogs

  摘要：

  一系列链支化的1,3-二苄基硫脲衍生物被设计、合成，并评估其对TRPV1的拮抗活性。合成的链支化1,3-二苄基硫脲9a-g通过使用新生大鼠培养脊髓感觉神经元的45Ca2+流入实验进行了拮抗活性测试。氟化乙基支化类似物9g表现出最强的拮抗活性，其IC50值为0.41 μM，但所有链支化类似物的活性均低于母体化合物MK-056和SC-0030，这表明B环苄基位置的链支化对活性有不利影响。优化的受体结合似乎受到链支化的干扰，导致活性降低。

  DOI：

  10.1007/s12272-012-0212-x

文献信息

• Catalytic Enantioselective Addition of Organometallic Reagents to <i>N</i>-Formylimines Using Monodentate Phosphoramidite Ligands
  作者：Maria Gabriella Pizzuti、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/jo702140f

  日期：2008.2.1

  The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozinc and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic α-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite

  据报道，通过芳族和脂肪族α-酰胺基砜原位生成的铜/次膦酸酯催化的有机锌和有机铝试剂向N-酰基嘧啶的加成反应，不对称合成了受保护的胺。获得了高产率的旋光性N-甲酰基保护的胺，对映选择性高达99％。在反应条件下，检测到亚磷酰胺配体被部分氧化为相应的磷酸酰胺。初步研究了其起源及其对催化加成反应的影响。
• Development of Chiral Catalysts by Asymmetric Activation for Highly Enantioselective Diethylzinc Addition to Imines
  作者：Liu-Zhu Gong、Hai-Le Zhang、Hua Liu、Xin Cui、Ai-Qiao Mi、Yao-Zhong Jiang

  DOI：10.1055/s-2005-863709

  日期：——

  derived from chiral 1,2-diphenyl-ethanene-1,2-diamine, BINOL derivatives, and diethylzinc are evaluated in the asymmetric addition of diethylzinc to N-acylimines. In the presence of 10 mol% L3ZnAl, high enantioselectivities and yields were provided for a wide range of aromatic imines in 1,2-dichloroethane at -25 °C.

  基于不对称活化概念，在不对称加成中评估了由衍生自手性 1,2-二苯基-乙烷-1,2-二胺、BINOL 衍生物和二乙基锌的二亚胺组合形成的原位手性锌配合物库二乙基锌转化为 N-酰基亚胺。在 10 mol% L3ZnAl 存在下，在 -25 °C 下，1,2-二氯乙烷中的多种芳族亚胺均具有高对映选择性和产率。
• Discovery of chiral catalysts by asymmetric activation for highly enantioselective diethylzinc addition to imines: using racemic and achiral diimines as effective activators
  作者：Hua Liu、Hai-Le Zhang、Shuang-Jun Wang、Ai-Qiao Mi、Yao-Zhong Jiang、Liu-Zhu Gong

  DOI：10.1016/j.tetasy.2005.07.014

  日期：2005.9

  A library of chiral zinc complexes formed in Situ by the combination of achiral and racemic diimines with 3,3'-di(3,5-ditrifluoromethylphenyl)-BINOL and diethylzinc were evaluated in the asymmetric addition of diethylzine to N-acylimines. In the presence of 10 mol % of chiral ligand 4 and racemic diimine 5, high enantioselectivities of up to 97% ee and yields of up to 96% were achieved for a wide range of aromatic imines in dichloromethane at -30 degrees C. (c) 2005 Elsevier Ltd. All rights reserved.
• Chain-branched 1,3-dibenzylthioureas as vanilloid receptor 1 antagonists
  作者：Chong Hyun Ryu、Mi Jung Jang、Jeong Wha Jung、Ju-Hyun Park、Hye Young Choi、Young-ger Suh、Uhtaek Oh、Hyeung-geun Park、Jeewoo Lee、Hyun-Joo Koh、Joo-Hyun Mo、Yung Hyup Joo、Young-Ho Park、Hee-Doo Kim

  DOI：10.1016/j.bmcl.2004.01.066

  日期：2004.4

  A series of chain-branched 1,3-dibenzylthiourea derivatives were synthesized, and tested their antagonist activity against vanilloid receptor 1. Chain-branching led to a significant change in the mode of action and the potency. (R)-Methyl or ethyl-branched 1,3-dibenzylthiourea derivatives showed the most potent antagonist activity up to the IC50 value of 0.05 muM which is 10-fold more potent than capsazepine. (C) 2004 Elsevier Ltd. All rights reserved.
• Chain branching approach in structure modification of TRPV1 receptor antagonist MK056 and its analogs
  作者：Mijung Jang、Chong Hyun Ryu、Young-Ho Park、Hee-Doo Kim

  DOI：10.1007/s12272-012-0212-x

  日期：2012.2

  A series of chain branched 1,3-dibenzylthiourea derivatives were designed, synthesized, and evaluated for their antagonist activity against TRPV1. The synthesized chain branched 1,3-dibenzylthioureas 9a-g were tested for their antagonist activities against TRPV1 by 45Ca2+-influx assay using neonatal rat cultured spinal sensory neurons. Fluorinated ethyl-branched analog 9g showed the most potent antagonist activity with an IC50 value of 0.41 μM, but all of the chain branched analogs were less potent than the parent compounds MK-056 and SC-0030, indicating that chain branching on the benzylic position of B-ring is detrimental to potency. Optimized receptor binding seems to be interfered by chain branching, and resulted in decrease in potency.

  一系列链支化的1,3-二苄基硫脲衍生物被设计、合成，并评估其对TRPV1的拮抗活性。合成的链支化1,3-二苄基硫脲9a-g通过使用新生大鼠培养脊髓感觉神经元的45Ca2+流入实验进行了拮抗活性测试。氟化乙基支化类似物9g表现出最强的拮抗活性，其IC50值为0.41 μM，但所有链支化类似物的活性均低于母体化合物MK-056和SC-0030，这表明B环苄基位置的链支化对活性有不利影响。优化的受体结合似乎受到链支化的干扰，导致活性降低。